Podcast Episode 6: Grace O’Malley, the Pirate Queen.

This Tale is a script for an episode of the Tales of History and Imagination podcast. Click here for the episode

Hi all thanks for joining me. Our tale begins today close to it’s chronological end, in September 1593. We’re at Greenwich palace, a now long demolished royal residence on the river Thames- it’s now the site of a naval hospital if anyone’s wondering- and there waits England’s fairy Queen, Elizabeth I. She’s there to meet with a rival queen who she has been at loggerheads with since 1574, her own fault as she has encroached on the latter queen’s lands from as early as 1558. No, if you’re wondering, we’re not talking of Mary Queen of Scots – at this point Mary was dead, in her grave for a little over 6 years, nor was she meeting with some Spanish Infanta. While making notes for this episode something the American philosopher Ralph Waldo Emerson said kept coming back up… Quote.

“Piracy and war gave place to trade, politics and letters; the war-lord to the law-lord; the privilege was kept, whilst the means of obtaining it were changed”

One queen, by Emerson’s reckoning would have been pretty much the Law lord, this is Elizabeth – Her ancestors had violently ascended the ladder to the top, and while her reign was notable for a number of battles, she had the privilege of letting others spill blood for her. Was she the stereotypically genteel image we would associate with her now? Not so much so. Elizabeth had rotten, brown teeth. Her skin was constantly covered in Venetian ceruse, a thick mask of white lead and vinegar, which must have smelled… like a mixture of white lead and vinegar. She wore this mask more to cover terrible pock marks left from a bout of smallpox, and the lead content may well have caused her death not too long after this tale. In itself venetian ceruse was known to have a disfiguring effect on others. I don’t intend to say this to be mean, but mention this as a number of tales paint the other queen as something far more savage – I am not convinced 21st century eyes would have viewed them that differently from one another.

The other queen, however was still very much a warlord, a bona fide pirate queen who made her name leading her ships into battle, raiding enemy ships and towns, and looting with the best of them. She knew how to fight with the best of them. The queen about to make dock was none other than Grace O’Malley, leader of the Irish region of Connaught. Today I want to look at her remarkable life, and how it lead to this fateful meeting. Welcome folks to Tales of History and Imagination, Season 1 Episode 6, Grace O’Malley- Pirate Queen.

(theme music Ishtar The Enemy Within)

Grace O’Malley, aka – and sorry I’m going to butcher some if not all of these Gaelic pronunciations- Grainne Mhaille was born some time around 1530 to Eoghan and Maeve Mhaille – John and Margaret in modern speak. Eoghan was the feudal lord of Umhaill, a territory in Connaught, now County Cork, Ireland. As a local aristocrat whose family held power in the area he was far more in the vein of the warlord than the law lord – He provided protection for the locals, taxed their income, and actively drew income as a privateer and occasional merchant. For all their lineage, it was their ability to inflict violence on any challenger which kept them at the top of the pile. In the West of Ireland they were well beyond the pale – the outer border of the Dublin region then under English rule, but during his lifetime Eoghan would see Elizabeth’s father Henry VIII encroach upon his land, till Henry had enough of the land to crown himself of King of Ireland in 1542. Grace would grow up viewing the English as the aggressive imperialists next door. Henry VIII would rule until his death in 1547, passing the crown to his 9 year old son, his only son, Edward VI, who in turn died in 1553 – the cause of death most likely the disease of the previous episode, tuberculosis. Lady Jane Grey, a relative from another branch of the family tree held the crown for nine days, before getting locked away in the tower of London. The crown then passed to Henry’s eldest daughter, Mary I, known as ‘Bloody Mary’ for her persecution of the protestants. She died of, likely ovarian or uterine cancer in 1558, passing the crown to Queen 1 in this tale, Elizabeth.

Queen Elizabeth I


Grace’s tale of her rise to power is quite different from Elizabeth’s. Eoghan had an elder son from a previous relationship, Donal na Piopa. Because he was considered the bastard son, the title would eventually pass to Grace. This was lucky for Connaught in a way; legend has it Donal was well liked, and a born entertainer who would break into song on the drop of a hat. He wasn’t interested in the piracy and pillaging that was his father’s stock and trade though. Grace on the other hand lived for the seven seas. From a young age she showed an interest in seafaring, and legend has it when she asked to join her father on a trading journey to Spain the other sailors laughed at her stating her long hair would get caught in the ropes. As a result she cut her hair off, embarrassing her father into let her go. It turned out she was a natural, and would regularly sail with her father after, learning the trade. Aged 16 she would marry Donal O’Flaherty, the son of another local chieftain, and would bear her first child with Donal at 17. Contrast to Elizabeth, she may have found love- it is most often suggested she was lovers with Robert Dudley, Earl of Leicester, and son of the guy who managed to put Lady Jane Grey on the throne for nine days – but she faced such a tangle of competing networks and interests it would have been very difficult for Elizabeth to ever marry, whether for love or otherwise – without upsetting some faction or other. Of course Grace’s marriage was not apolitical though – it led to the consolidation of quite a large region under one family. She would have two sons and a daughter with Donal, and for a time retired from the sea. She did not have a long marriage to Donal. In the 1560’s, I have read a dozen books and articles and anywhere from 1560 to 1565 are quoted (1560 seems most trustworthy however) – Donal came to a messy end fighting with the neighboring Joyce clan over a long disputed castle on the shores of Lough Corrib. Grace, ever the warrior queen, retaliated – invading the castle and ousting the Joyces. While many in the tribe were impressed by how capable Grace was as a military leader, sexism came into play and Donal’s titles and land were passed to a cousin. She returned to her family with a small army in tow, set herself up on nearby Clare Island, and returned to piracy – something she later described to Elizabeth as ‘maintenance by land and sea’, I guess in a way similar to how Tony Soprano summed his work up as ‘waste management’? Now in time she would pick up her father’s titles however, and her sons recapture their father’s lost chieftainship.



As with much of Grace’s life, there is little by way of documentation as to what specifically she was doing at this point, but what exists shows she had put together a standing army of 200, with which she would do battle with certain neighboring chiefs, as well as carrying out regular raids along the coasts of Scotland. She had a business transporting ‘Gallowglasses’, Scottish mercenaries, to Ireland for allied chieftains in their battles, and according to one 1593 report from an English governor, had begun fomenting an opposition to English encroachment by this time. One story which does survive from this time, in 1565 a ship floundered off nearby Achill Head, on a particularly stormy day. Looking to salvage whatever she could from the wreck Grace set off into the storm. The texts I have read don’t say what treasure she may have found there, but she did find one Hugh De Lacey, shipwrecked sailor and son of a Wexford merchant. Grace took Hugh as a lover, but not for long, as he was killed by the McMahon clan. Enraged, Grace took revenge on the McMahons, murdering the perpetrators and taking over their castle, Doona, on the coast of Erris. The tales don’t make much of her being now twice unlucky in love, but all point out she now had two strategic points where she could capture a lot of passing booty – and it is at this point that she begins to become both very well known, and extremely wealthy.

Much of her tale at this time really is more folklore than history. One tale has it that Grace chased one neighboring chieftain who had tried to steal from her to a small island which contained just a church and a hermit. When the chieftain took refuge in the church Grace besieged the church and threatened to stay there till he starved to death if need be, but the chieftain dug a tunnel to safety. This is generally brought up to point out how godless Grace was, apparently.

One tale which was meant to show her in a different light goes as follows. One night returning from a raid Grace found herself needing to take rest at the town of Howth, near Dublin. They had run low on provisions and needed water particularly to get them home. She called upon the local lord, St Lawrence Earl of Howth, only to find the castle gates locked and a porter with a message that the Earl is not to be disturbed. He was dining. Sent packing she just so happened to come across the Earl’s grandson, and on a whim, kidnapped the boy. They boarded and headed for home. Not too long after they were visited by the Earl himself, distraught and willing to pay any price for the boy’s return. Grace agreed to his return, not for money but for a promise that in future the Earl would always leave his castle gates open to visitors, and when he dined he would always keep a chair free, for any passing traveler who stopped by – a tradition which remains to this day. The sources tell this as an example of her daring and level headedness- I think it is an interesting window into the heavily honor bound society she lived in where small sleights would often escalate into clan warfare, to a degree does show some level headedness – and does serve as a reminder of how different a time they lived in than us. One just has to think back to the Chibok schoolgirl kidnappings in Nigeria April 14 2014- by members of Boko Haram – and the subsequent worldwide condemnation of the act. We’re not so quick to make heroes of kidnappers these days.

In 1566 she remarried, to another chieftain, Richard ‘Iron Dick’ – for his ironworks of course – Bourke. While married to Bourke she continued a life of plunder – story has it they soon divorced, but not before bearing Richard a son – known as Toby of the Ships as he was born onboard a ship while away pirating. Legend has it that a day after giving birth, somewhere off the Irish coast they were boarded by Barbary pirates of Algerian origin who had strayed a long way from home. These Barbary picaroons were shocked to find themselves greeted by this half naked, angry lady with a musket – furious not just by their presence but that they dare arrive while she was breastfeeding. They fled for their lives. Grace O’Malley’s life continued in much this manner till 1574, which we’ll discuss right after this break.

(break music)

Hi folks welcome back, so things take a turn for the worse around 1574. Now one might appreciate when Henry VIII laid claim to Ireland in 1542 it was largely a nominal thing, not of any great importance to people beyond the area which England controlled – the area known as the pale. Without digressing too far, when he made the proclamation it was not too long after England had officially brought Wales in, ad he had turned his attentions to Scotland. In 1544 Henry found himself at war with France, and soon after all but bankrupt from that war. Had he lived longer he may have taken a shot at the 60 independent chieftains in Ireland, but the stars were never to align for Henry. For Elizabeth, she would move in that direction, but didn’t make any serious moves against the O’Malleys’ until they became too big a problem to ignore anymore. This would happen in 1576.

Now this is not to say Elizabeth I didn’t think of an all out takeover of Ireland before this time. In 1565 it was mooted. Catholic Spain began to get very concerned over growing protestant numbers in the Netherlands, then under their control. Protestant England started to worry about a Spanish invasion, and the very real possibility they would take over Ireland as a home base. England didn’t have the resources at the time to launch an invasion – though they had a number of subjects they could resettle there, just to make the place more English. Like any colonization this meant an arrival of second sons of the gentry intent on building a fortune for themselves denied by primogeniture – the practice of passing everything to the first born son, of chancers, adventurers, and of the kind of bad men who can facilitate a land grab off the locals. Ireland quickly found itself overrun by these craven, desperate characters who viewed the native Irish in much the same way as the Spanish Conquistadors say, or the Jamestown settlers viewed the people of the Americas- savage, backwards, and unless you were talking about them as a cheap source of labour – then they were otherwise an impediment to progress. By 1569, in spite of active opposition by the chieftains, the English had established a military Governor – Sir Edward Fitton- to wield a big stick in Connaught. He had backing by a counterpart in Sir John Perot, in Munster. Both men had sizeable military support, and they began to work out how they would carve up Grace’s kingdom.

Many of the chieftains put up a resistance. The MacWilliam of Mayo (something like a chief of chiefs), the O’Flaherty’s, Richard Bourke, and the O’Malley’s included. The MacWilliam had given in by his death in 1570, handing much of Connaught to the English. In the face of an opposition still choosing to scrap it out, in 1576 the English Lord Deputy, Sir Henry Sidney, arrived in Connaught to make the chieftains an offer they couldn’t refuse. Stop fighting now. Pledge allegiance to the crown, including paying the crown tax and complying to their laws. Get rid of the Gallowglasses in the area. Provide a contingent of Irish soldiers to the crown. If you doo all of this you will get your titles back, and some of your land. If you choose to keep fighting, then the offer is off the table. This was put to the chieftains in a meeting in Galway. In 1577 Grace met with Henry Sidney and pledged her allegiance to the crown. She also spent quite some time in conversation with Henry’s son, the poet Sir Philip Sidney – who recorded how remarkable he found O’Malley, but not what they discussed. In a book of his aphorisms collated long after his death Sir Philip Sydney would say “The only disadvantage of an honest heart is credulity.” He may have felt more than a little credulous, foolish – when almost immediately afterward she launched a raid on a rival chief, the Earl of Desmond, who had sold out to the English early on in the piece. This raid did not go as well as her raids usually did however, and Grace was captured and jailed for 18 months for the attack. In 1581 both her and Richard Bourke officially pledged their fealty, and were rewarded with British titles, and things may have settled to a point – no doubt the two would continue to provide low key resistance, but Ireland would likely have remained a safe place for the British colonizers and the sell outs – but in 1584 a new governor arrived. The new governor was a hard nosed ball breaker by the name of Sir Richard Bingham – yes the same family as the later John Bingham, Lord Lucan – who became infamous in 1974 when he botched a murder attempt on his wife, killing the nanny – then disappearing without a trace. Well Richard Bingham was determined to put down all opposition whatsoever by the chieftains, and he saw Grace O’Malley as especially dangerous.

The villianous Sir Richard Bingham.



Bingham, first undermined Grace’s title – which he saw largely based on her marriage to Bourke (their divorce was only temporary), Bourke died in 1583, leaving Grace yet again a widow, and now ruled by a law which stripped widows of their titles in favour of their children. He then went after her children – murdering her eldest son Owen, having two of Richard Bourke’s sons from his previous marriage executed for treason, kidnapping the beloved youngest child, Toby of the ships – and finally Bingham had Grace arrested with the intent of having her executed also. Grace’s son in law offered himself up in Grace’s place, which Bingham did allow, for some reason. Seizing the opportunity Grace O’Malley loaded up a ship, and out of desperation sailed for London. She knew she could not fight Bingham – he had been using similar tactics with other chieftains, decimating all opposition – but she knew Bingham had a boss – a lady who, like her had made it to the top of the ladder in a system which heavily favoured men. She was somewhere around the same age Grace is believed to have been born in 1530, Elizabeth in 1536. For their warlord- law lord divide they must have experienced similar trials and tribulations. She might just be willing to talk queen to queen.

Which brings us full circle- back to that meeting at Greenwich palace in September 1593. As typical of much of this story, their meeting wasn’t sufficiently recorded. We don’t know the specifics of their conversation, though we do know they did have a long conversation in Latin- Grace spoke no English, Elizabeth no Gaelic- both spoke the lingua franca of the time however. We know they were expecting Grace to show up looking like a stereotypical peasant, but when she arrived she had recently bathed – no mean feat in Elizabethan England – but that is a whole other topic. She also showed up wearing a fine gown to rival any courtier – although she caused a scandal when she refused to bow to Elizabeth, was found to have a knife on her ‘for her protection’ and, at one point had Elizabeth’s court horrified when she took a lace handkerchief from a lady in waiting to blow her nose -then disposed of the handkerchief in a lit fireplace. We do know she did state she was a loyal subject who was being unfairly targeted by Bingham – who had robbed her of her title, lands, even her extensive herd of cattle. She argued that Bingham was stopping her pursuit of legitimate maritime business, and holding her son captive. Elizabeth sided with Grace, ordering Bingham to leav her and her family alone – and to release Toby of the ships immediately. Grace, now well into her 60s, did return to piracy – leading to further conflict with Sir Richard Bingham. Again Grace returned to see Queen Elizabeth, in 1595 – this time not just getting her backing, but for a time getting Bingham removed from his post. Though this was very far from a happily ever after for the people of Connaught – it did not take a terribly long time for Bingham to regain his title, and things would only go from bad to worse for the Irish – Grace O’Malley, a warrior pirate queen who lived by the sword would live to a ripe old age for those times of 72, and die of natural causes in 1603 – the same year that Elizabeth I passed on.

Thank you for tuning in all, this one is a bit of a personal one for me – though I’m no aristocrat I do have family ties back to Ireland- and according to a DNA test have quite a bit of blood from Connaught. I’ll be back on the podcast in a few weeks’ time with a new tale. I will have a new blog post up on the in between week at historyandimagination.com. Please like, share, follow us on Facebook – or Instagram, both under Tales of History and Imagination. If you liked this episode please share us around.
Music this week as always provided by Ishtar- a former New Zealand based hard rock group who, if they could be Grace O’Malley or Elizabeth I would have been Grace any day. Take care folks we’ll be back soon.

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